WO2014138490A1 - Synthetic lipochitooligosaccharide analogs for enhancing plant performance - Google Patents
Synthetic lipochitooligosaccharide analogs for enhancing plant performance Download PDFInfo
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- WO2014138490A1 WO2014138490A1 PCT/US2014/021428 US2014021428W WO2014138490A1 WO 2014138490 A1 WO2014138490 A1 WO 2014138490A1 US 2014021428 W US2014021428 W US 2014021428W WO 2014138490 A1 WO2014138490 A1 WO 2014138490A1
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- UCMLSEINWYQAES-UHFFFAOYSA-N COC(C(C1O)N)OC(CO)C1O Chemical compound COC(C(C1O)N)OC(CO)C1O UCMLSEINWYQAES-UHFFFAOYSA-N 0.000 description 1
- AMYRXFODJCDLSX-AATRIKPKSA-N COC(C(C1O)NC(/C=C/C(C2)=CC=CC2C(F)(F)F)=O)OC(CO)C1O Chemical compound COC(C(C1O)NC(/C=C/C(C2)=CC=CC2C(F)(F)F)=O)OC(CO)C1O AMYRXFODJCDLSX-AATRIKPKSA-N 0.000 description 1
- KSBWHDDGWSYETA-SNAWJCMRSA-N OC(/C=C/c1cccc(C(F)(F)F)c1)=O Chemical compound OC(/C=C/c1cccc(C(F)(F)F)c1)=O KSBWHDDGWSYETA-SNAWJCMRSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
Definitions
- the invention relates to synthetic compounds for enhancing plant performance.
- Lipochitooligosacchandes are naturally made in rhizobial bacteria and function as nodulation factors which increase productivity of a variety of crops, including soybeans, peanuts, alfalfa, and dry beans.
- the nodulation factor lipochitooligosacchandes have a backbone of four or five ⁇ 1 ,4-linked N-acylated glucosamine residues, a structure also found in chitin (poly-[1 -4]- -N-acetyl-D-glucosamine). This backbone is N- acylated and can carry diverse substitutions at both ends, depending on the rhizobial species in which it is made.
- the /V-acylation of the terminal unit is with fatty acids of general lipid metabolism such as vaccenic acid (C18:1 A1 1 Z) and in other rhizobia the /V-acylation is with polyunsaturated fatty acids such as C20:3 and C18:2.
- the nodulation factor lipochitooligosaccharides made in any one species of bacteria are a mixture of compounds having different substitutions that are not possible to completely separate. Preparations of lipochitooligosaccharides produced through biological means have variable activity.
- Some nodulation factor lipochitooligosaccharides have been chemically synthesized. There are various reported methods for making small samples of lipochitooligosaccharides, for example as described in Nicolaou et al., J. Am. Chem. Soc. 1 14: 8701 -8702 (1992); Ikeshita et al., Carbohydrate Research C1 -C6 (1995); and Wang et al., J. Chem. Soc. Perkin Trans. 1 : 621 -628 (1994). US 8049002 discloses a process of synthesizing individual lipochitooligosaccharide analogs that is amenable to large scale production.
- US 8,198,420 discloses synthetic compounds which are active as nodulation factors and as plant growth stimulators, that have an aromatic ring attached to an oligosaccharide, and a carbon chain attached to the aromatic ring.
- One aspect of the present invention provides a compound having the structure (I)
- n 1 - 20;
- n 0, 1 , 2, 3 or 4;
- A is selected from -C(O)-, -C(S)-, C(O)O-, -C(O)S-, -C(S)S-;
- D is selected from H, CH 3 , and a linear or branched, saturated or unsaturated, hydrocarbon-based chain containing from 2 to 20 carbon atoms;
- E is selected from OH, NH 2 , and NHC(O)CH 3 ;
- R 1 is selected from H and C1 -20 alkyl
- R 2 is selected from a linear or branched, saturated or unsaturated, hydrocarbon-based chain containing from 1 to 20 carbon atoms, arylene, or substituted arylene;
- R 3 and R 4 are independently selected from C1 -6 alkyl, a halogen, and an aryl;
- R 5 , R 6 and R 7 are independently selected from H, -C1 -6 alkyl, - C(0)C1 -6 alkyl, -C(S)C1 -6 alkyl, -C(0)OC1 -6 alkyl, -C(O)NH 2 , -C(S)NH 2 , - C(NH)NH 2 , -C(O)NHC1 -6 alkyl, -C(S)NHC1 -6 alkyl, and -C(NH)NHC1 -6 alkyl.
- Another aspect of the present invention provides an agricultural composition comprising a compound of the structure (I).
- Another aspect of the present invention provides a method of treating plant material comprising:
- compositions comprising, “comprising,” “includes,” “including,” “has,” “having,” “contains” or “containing,” or any other variation thereof, are intended to cover a non-exclusive inclusion.
- a composition, a mixture, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, method, article, or apparatus.
- “or” refers to an inclusive or and not to an exclusive or.
- a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
- the indefinite articles "a” and "an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component.
- invention or "present invention” as used herein is a non- limiting term and is not intended to refer to any single embodiment of the particular invention but encompasses all possible embodiments as described in the specification and the claims.
- the term "about” modifying the quantity of an ingredient or reactant of the invention employed refers to variation in the numerical quantity that can occur, for example, through typical measuring and liquid handling procedures used for making concentrates or use solutions in the real world; through inadvertent error in these procedures; through differences in the manufacture, source, or purity of the ingredients employed to make the compositions or carry out the methods; and the like.
- the term “about” also encompasses amounts that differ due to different equilibrium conditions for a composition resulting from a particular initial mixture. Whether or not modified by the term “about”, the scope of the claims is intended to encompass equivalents to the quantities.
- the term “about” means within 10% of the reported numerical value, preferably within 5% of the reported numerical value.
- plant growth or "plant performance” as used herein refers to measures of plant development such as seed germination, seedling emergence, early radical or root and shoot growth, plant height, time to flowering, tillering (for grasses), days to maturity, vigor, biomass and yield.
- propagating material means a seed or regenerable plant part.
- regenerable plant part means a part of the plant other than a seed from which a whole plant may be grown or regenerated when the plant part is placed in agricultural or horticultural growing media such as moistened soil, peat moss, sand, vermiculite, perlite, rock wool, fiberglass, coconut husk fiber, tree fern fiber, and the like, or even a completely liquid medium such as water.
- Regenerable plant parts commonly include rhizomes, tubers, bulbs and corms of such geophytic plant species as potato, sweet potato, yam, onion, dahlia, tulip, narcissus, etc.
- Regenerable plant parts include plant parts that are divided (e.g., cut) to preserve their ability to grow into a new plant.
- regenerable plant parts include viable divisions of rhizomes, tubers, bulbs and corms which retain meristematic tissue, such as an eye. Regenerable plant parts can also include other plant parts such as cut or separated stems and leaves from which some species of plants can be grown using horticultural or agricultural growing media.
- seed includes both unsprouted seeds and seeds in which the testa (seed coat) still surrounds part of the emerging shoot and root.
- Foliage as defined in the present application includes all aerial plant organs, that is, the leaves, stems, flowers and fruit.
- rhizosphere refers to the area of soil that immediately surrounds and is affected by the plant's roots.
- treating means applying a biologically effective amount of a plant performance enhancing compound, or a composition containing the compound, to a seed or other plant
- biologically effective amount refers to that amount of a substance required to produce a desired effect on plant growth and yield. Effective amounts of the composition will depend on several factors, including treatment method, plant species, propagating material type and environmental conditions.
- agricultural composition refers to one or more substances formulated for at least one agricultural application.
- Agricultural applications are any application that enhances plant performance, such as, for example, germination improvement, growth improvement, yield improvement, pest control, disease control and resistance to abiotic environmental stress.
- alkyl means a linear or branched hydrocarbon group up to and including 20 carbon atoms. Common examples of such alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, isobutyl, pentyl, neopentyl, hexyl, heptyl, isoheptyl, 2-ethylhexyl, cyclohexyl and octyl.
- aryl is known in the art to mean a group defined as a monovalent radical formed conceptually by removal of a hydrogen atom from a hydrocarbon that is structurally composed entirely of one or more benzene rings.
- hydrocarbons include benzene, biphenyl, terphenyl, naphthalene, phenyl naphthalene, and naphthylbenzene.
- Aryl groups include aromatic carbocyclic groups having a single ring (e.g., phenyl), multiple rings (e.g., biphenyl), or multiple condensed rings in which at least one is aromatic, (e.g., 1 ,2,3,4-tetrahydronaphthyl, naphthyl, anthryl, or phenanthryl), which is optionally mono-, di-, or trisubstituted with, e.g., halogen, lower alkyl, lower alkoxy, lower alkylthio, trifluoromethyl, lower acyloxy, aryl , heteroaryl, and hydroxy.
- aromatic carbocyclic groups having a single ring (e.g., phenyl), multiple rings (e.g., biphenyl), or multiple condensed rings in which at least one is aromatic, (e.g., 1 ,2,3,4-tetrahydronaphthyl, naphthyl, anthryl,
- heteroaryl groups wherein heteroaryl is defined as 5-, 6-, or 7-membered aromatic ring systems having at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur.
- heteroaryl groups are pyridyl, pyrimidinyl, pyrrolyl, pyrazolyl, pyrazinyl, pyridazinyl, oxazolyl, furanyl, quinolinyl, isoquinolinyl, thiazolyl, and thienyl, which can optionally be substituted with, e.g., halogen, lower alkyl, lower alkoxy, lower alkylthio, trifluoromethyl, lower acyloxy, aryl, heteroaryl, and hydroxy.
- “Monoalkenyl” or “monoalkynyl” as used herein refers to the presence of a double or triple bond connecting two carbon atoms.
- Dialkenyl or polyalkenyl refers to the presence of two or more double bond connected carbon atoms, respectively.
- Polyalkynyl refers to two or more triple bond connected carbon atoms.
- unsubstituted arylene refers to an arylene that has no substituents.
- the arylene can be , a heteroarylene, comprising one or two hetero atoms selected from nitrogen, oxygen, and sulfur; a
- naphthylene a heteronaphthylene comprising one or two hetero atoms selected from nitrogen, oxygen, and sulfur; a divalent radical derived from two fused aromatic or hetero aromatic rings containing five or six atoms each and comprising one or two hetero atoms selected from nitrogen, oxygen, and sulfur; a biphenylene; and a heterobiphenylene comprising one or two hetero atoms selected from nitrogen, oxygen, and sulfur.
- substituted arylene refers to an arylene with one or more substituents.
- the arylene may be a heteroarylene as described above
- Embodiments of the present invention include compounds that are synthetic lipochitooligosaccharide analogs (SLA), compositions containing the compounds, and the use of the compounds to enhance plant performance.
- SLA synthetic lipochitooligosaccharide analogs
- the compounds are of the general structure (I):
- n 1 - 20;
- n 0, 1 , 2, 3 or 4;
- A is selected from -C(O)-, -C(S)-, C(O)O-, -C(O)S-, -C(S)S-;
- C is a substituted or unsubstituted arylene wherein there are zero, one, two, three, or four substituents that are independently selected from a halogen, -CN, -C(O)OR 5 , -C(O)NR 6 R 7 , -CF 3 , -OCF 3 , -NO 2 , -N 3 , -OR 5 , - SR 5 , -NHR 6 , -NR 6 R 7 , and -C1 -6 alkyl;
- D is selected from H, CH 3 , and a linearand branched, saturated and unsaturated, hydrocarbon-based chains containing from 2 to 20 carbon atoms;
- E is selected from OH, NH 2 , and NHC(O)CH 3 ;
- R 1 is selected from H and C1 -20 alkyl
- R 2 is selected from linear and branched, saturated and unsaturated, hydrocarbon-based chains containing from 1 to 20 carbon atoms, arylene, or substituted arylene;
- R 3 and R 4 are independently selected from C1 -6 alkyl, a halogen, and an aryl;
- R 5 , R 6 and R 7 are independently selected from H, -C1 -6 alkyl, - C(O)C1 -6 alkyl, -C(S)C1 -6 alkyl, -C(O)OC1 -6 alkyl, -C(O)NH 2 , -C(S)NH 2 , - C(NH)NH 2 , -C(O)NHC1 -6 alkyl, -C(S)NHC1 -6 alkyl, and -C(NH)NHC1 -6 alkyl.
- the substituted arylene of R 2 may be substituted with one or more substituents independently selected from: halogen, CN, C(O)OR 5 , C(O)NR 6 R 7 , CF 3 , NO 2 , C1 -6 alkyl, mannose, glycerol, -C(O)C1 -6 alkyl, -C(S)C1 -6 alkyl, -C(O)OC1 -6 alkyl, -C(O)NH 2 , - C(S)NH 2 , -C(NH)NH 2 , -C(O)NHC1 -6 alkyl, -C(S)NHC1 -6 alkyl, and - C(NH)NHC1 -6 alkyl.
- substituents independently selected from: halogen, CN, C(O)OR 5 , C(O)NR 6 R 7 , CF 3 , NO 2 , C1 -6 alkyl, mannose, glycerol,
- the carbon chain of a aryl containing aliphatic carboxylic acid is attached directly to an amine substituent of an oligosaccharide, at the terminal amine-sugar unit. There is no aromatic ring between the carbon chain and the amine.
- the carbon chain is unsaturated, containing at least one alkenyl or one alkynyl group. There is an aromatic ring structure at the end of the carbon chain, which may itself have substituents, and is not directly attached to the oligosaccharide.
- the triple and/or double bonds may occur at any positions in the carbon chain that are chemically feasible.
- a compound of structure (I) has one or more of the following substituents:
- n 1 or 2;
- n 0 or 1 ;
- A is -C(O)-
- C is an arylene substituted with one or more substituents selected from halogen, CN, CF 3 , NO2, and C1 -6 alkyl;
- D is selected from H, CH 3 , and a linear and branched, saturated and unsaturated, hydrocarbon-based chains containing from 2 to 15 carbon atoms;
- E is NHC(O)CH 3 ;
- R 1 is selected from H and CH 3 ;
- R 2 is CH 3 or phenylene.
- a compound of structure (I) has all of the following characteristics:
- n 1 or 2;
- n 0;
- A is -C(O)-
- C is an arylene substituted with one or more substituents selected from halogen, CN, CF 3 , NO 2 , and C1 -6 alkyl;
- D is selected from H, CH 3 , and a linear and branched, saturated and unsaturated, hydrocarbon-based chains containing from 2 to 15 carbon atoms;
- R 1 is selected from H and CH 3 ;
- R 2 is CH 3 or phenylene.
- Compounds of structure (I) can be synthesized by combining an aryl-containing aliphatic carboxylic acid acid of the desired structure, terminating with adesired substituted aromatic ring, and a desired oligosaccharide-amine, in the presence of 1 -(3-dimethylaminopropyl)-3- ethylcarbodiimide (EDC) and 4-dimethylaminopyridine (DMAP). Typically the reaction is stirred overnight at room temperature, pumped dry, and the product is washed with water and dried. Synthesis of representative SLAs of structure (I) is described in examples herein.
- aryl-containing aliphatic carboxylic acid acids are commercially available, for example from Alfa Aesar (Ward Hill, MA), 3B Scientific Corporation (Libertyville, IL), AK Scientific, Inc. (Union City, CA), and Aldrich Sigma (St. Louis, MO). If not commercially available, a desired acid can be synthesized starting with a commercially available alcohol, which can be obtained, for example, from the same sources given above. The alcohol is oxidized into aldehyde which is further reacted with a ylide to produce an alpha, beta-unsaturated ester.
- oligosaccharide-amines can be synthesized as disclosed in US 8049002, from commercial available D-glucosamine hydrochloride. For example, synthesis of oligoglucosamines is disclosed in US 8049002.
- a compound of structure (I) is applied as a seed treatment formulation.
- Such formulations typically contain from about 10 "5 M to 10 "12 M of the compound of structure (I).
- formulations contain from about 10 "6 M to 10 "10 M of the compound.
- the locus of the propagating materials can be treated with the compound by many different methods. All that is needed is for a biologically effective amount of the compound of structure (I) to be applied on or sufficiently close to the propagating material so that it can be absorbed by the propagating material.
- the compound can be applied by such methods as drenching the growing medium including a propagating material with a solution or dispersion of the compound, mixing the compound with growing medium and planting a propagating material in the treated growing medium (e.g., nursery box treatments), or various methods of propagating material treatment whereby the compound of structure (I) is applied to a propagating material before it is planted in a growing medium.
- a compound of structure (I) is present as an active ingredient in an agricultural composition.
- composition is typically a formulation that includes an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent and a surfactant.
- an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent and a surfactant.
- a wide variety of formulations are suitable for the agricultural compositions; the most suitable types of formulations depend upon the method of application being used.
- Formulations may include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including
- microemulsions and/or suspoemulsions and the like which optionally can be thickened into gels.
- Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble.
- Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
- Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
- the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.
- Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Emulsifiers and Detergents and McCutcheon's Functional Materials (North America and International Editions, 2001 ), The Manufactuing Confection Publ. Co., Glen Rock, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
- Surfactants include, for example, ethoxylated alcohols, ethoxylated alkylphenols, ethoxylated sorbitan fatty acid esters, ethoxylated amines, ethoxylated fatty acids, esters and oils, dialkyl sulfosuccinates, alkyl sulfates, alkylaryl sulfonates, organosilicones, ⁇ /,/V-dialkyltaurates, glycol esters, phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and block polymers including polyoxyethylene/polyoxypropylene block copolymers.
- Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
- Liquid diluents include, for example, water, ⁇ /,/V-dimethylformamide, dimethyl sulfoxide, /V-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol.
- Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill.
- Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084.
- Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 and following, and PCT
- Pellets can be prepared as described in U.S. 4,172,714.
- Water-dispersible and water-soluble granules can be prepared as disclosed in U.S. 4,144,050, U.S. 3,920,442 and
- Tablets can be prepared as disclosed in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as disclosed in GB 2,095,558 and U.S. 3,299,566.
- compositions used for treating propagating materials, or plants grown therefrom can also comprise (besides the compound of structure (I)) an effective amount of one or more other biologically active
- Suitable additional compounds or agents include, but are not limited to, insecticides, fungicides, nematocides, bactericides, acaricides, entomopathogenic bacteria, viruses or fungi, growth regulators such as rooting stimulants, chemosterilants, repellents, attractants, pheromones, feeding stimulants and other signal compounds including apocarotenoids, flavonoids, jasmonates and strigolactones (Akiyama, et al., in Nature, 435:824-827 (2005); Harrison, in Ann. Rev. Microbiol., 59:19-42 (2005); Besserer, et al., in PLoS Biol., 4(7):e226 (2006);
- insecticides such as abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr,
- chlorfluazuron chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan,
- metconazole metominostrobin/fenonninostrobin (SSF-126), metrafenone (AC 375839), myclobutanil, neo-asozin (ferric methanearsonate), nicobifen (BAS 510), orysastrobin, oxadixyl, penconazole, pencycuron,
- probenazole prochloraz, propamocarb, propiconazole, proquinazid (DPX- KQ926), prothioconazole (JAU 6476), pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienoch
- Preferred insecticides and acaricides for mixing or formulating with compounds of structure (I) include pyrethroids such as cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and
- neuronal sodium channel blockers such as indoxacarb, insecticidal macrocydic lactones such as spinosad, abamectin, avermectin and emamectin; ⁇ -aminobutyric acid (GABA) antagonists such as endosulfan, ethiprole and fipronil; insecticidal ureas such as flufenoxuron and triflumuron; juvenile hormone mimics such as diofenolan and pyriproxyfen; pymetrozine; and amitraz.
- GABA ⁇ -aminobutyric acid
- Preferred biological agents for mixing with the present compounds include Bacillus thuringiensis and Bacillus thuringiensis delta- endotoxin as well as naturally occurring and genetically modified viral insecticides including members of the family Baculoviridae as well as entomophagous fungi.
- Preferred plant growth regulators for mixing or formulating with the compounds of structure (I) in compositions for treating stem cuttings are 1 H-indole-3-acetic acid, 1 H-indole-3-butanoic acid and 1 - naphthaleneacetic acid and their agriculturally suitable salt, ester and amide derivatives, such as 1 -napthaleneacetamide.
- Preferred fungicides for mixing with the structure (I) compounds include fungicides useful as seed treatments such as thiram, maneb, mancozeb and captan.
- formulations can provide compound of structure (I), generally after dilution with water, in solution or as particles small enough to remain dispersed in the liquid.
- Water-dispersible or soluble powders, granules, tablets, emulsifiable concentrates, aqueous suspension concentrates and the like are formulations suitable for aqueous drenches of growing media. Drenches are most satisfactory for treating growing media that have relatively high porosity, such as light soils or artificial growing medium comprising porous materials such as peat moss, perlite, vermiculite and the like.
- the drench liquid comprising the compound of structure (I) can also be added to a liquid growing medium (i.e.
- the amount of the compound of structure (I) needed in the drench liquid for efficacy i.e. biologically effective amount
- concentration of the compound of structure (I) in the drench liquid is generally between about 10 "5 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
- concentration of the compound of structure (I) in the drench liquid is generally between about 10 "5 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
- a compound of structure (I) can also be applied by mixing it as a dry powder or granule formulation with the growing medium. Because this method of application does not require first dispersing or dissolving in water, the dry powder or granule
- a formulation containing a compound of structure (I) is most efficiently applied concurrently with propagating material planting (e.g., seeding).
- propagating material planting e.g., seeding
- the formulation most conveniently a granule formulation
- the formulation is applied directly behind the planter shoe.
- T- band application the formulation is applied in a band over the row behind the planter shoe and behind or usually in front of the press wheel.
- the concentration of compound of structure (I) in the growing medium locus is generally between about 10 "5 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 " 10 M.
- concentration of compound of structure (I) in the growing medium locus is generally between about 10 "5 M to 10 "12 M of the composition, more typically between about 10 "6 M to 10 " 10 M.
- One skilled in the art can easily determine the biologically effective amount necessary for the desired level of efficacy.
- a propagating material can be directly treated by soaking it in a solution or dispersion of a compound of structure (I). Although this application method is useful for propagating materials of all types, treatment of large seeds (e.g., having a mean diameter of at least 3 mm) is more effective than treatment of small seeds for providing efficacy.
- Treatment of propagating materials such as tubers, bulbs, corms, rhizomes and stem and leaf cuttings also can provide effective treatment of the developing plant in addition to the propagating material.
- the formulations useful for growing-medium drenches are generally also useful for soaking treatments.
- the soaking medium comprises a nonphytotoxic liquid, generally water-based although it may contain nonphytotoxic amounts of other solvents such as methanol, ethanol, isopropanol, ethylene glycol, propylene glycol, propylene carbonate, benzyl alcohol, dibasic esters, acetone, methyl acetate, ethyl acetate, cyclohexanone, dimethylsulfoxide and /V-methylpyrrolidone, which may be useful for enhancing solubility of the compound of structure (I) and penetration into the propagating material.
- a surfactant can facilitate wetting of the propagating material and penetration of the compound.
- the amount of the compound needed in the soaking medium for efficacy i.e.
- the concentration of the compound of structure (I) in the soaking liquid is generally between about 10 "5 M to10 "12 M of the composition, more typically between about 10 "6 M to 10 "10 M.
- the soaking time can vary from one minute to one day or even longer.
- the propagating material can remain in the treatment liquid while it is germinating or sprouting (e.g., sprouting of rice seeds prior to direct seeding).
- the shoot and root directly contact the solution comprising the compound of structure (I).
- a propagating material can also be coated with a composition comprising a biologically effective amount of a compound of structure (I).
- the coatings of the invention are capable of effecting a slow release of the compound by diffusion into the propagating material and surrounding medium. Coatings include dry dusts or powders adhering to the
- Coatings can also be prepared from suspension
- compositions preferably include ingredients promoting adhesion of the coating to the propagating material.
- the compositions may also contain surfactants promoting wetting of the propagating material.
- Solvents used must not be phytotoxic to the propagating material; generally water is used, but other volatile solvents with low phytotoxicity such as methanol, ethanol, methyl acetate, ethyl acetate, acetone, etc. may be employed alone or in combination. Volatile solvents are those with a normal boiling point less than about 100 °C. Drying must be conducted in a way not to injure the propagating material or induce premature germination or sprouting.
- the thickness of coatings can vary from adhering dusts to thin films to pellet layers about 0.5 to 5 mm thick.
- Propagating material coatings of this invention can comprise more than one adhering layer, only one of which need comprise a compound of structure (I).
- Generally pellets are most satisfactory for small seeds, because their ability to provide a biologically effective amount of the compound is not limited by the surface area of the seed, and pelleting small seeds also facilitates seed transfer and planting operations. Because of their larger size and surface area, large seeds and bulbs, tubers, corms and rhizomes and their viable cuttings are generally not pelleted, but instead coated with powders or thin films.
- Propagating materials contacted with compounds of structure (I) in accordance to this invention include seeds.
- Suitable seeds include seeds of wheat, durum wheat, barley, oat, rye, maize, sorghum, rice, wild rice, cotton, flax, sunflower, soybean, garden bean, lima bean, broad bean, garden pea, peanut, alfalfa, beet, garden lettuce, rapeseed, cole crop, turnip, leaf mustard, black mustard, tomato, potato, pepper, eggplant, tobacco, cucumber, muskmelon, watermelon, squash, carrot, zinnia, cosmos, chrysanthemum, sweet scabious, snapdragon, gerbera, babys- breath, statice, blazing star, lisianthus, yarrow, marigold, pansy, impatiens, petunia, geranium and coleus.
- Propagating materials contacted with compounds of structure (I) in accordance to this invention also include rhizomes, tubers, bulbs or corms, or viable divisions thereof.
- Suitable rhizomes, tubers, bulbs and corms, or viable divisions thereof include those of potato, sweet potato, yam, garden onion, tulip, gladiolus, lily, narcissus, dahlia, iris, crocus, anemone, hyacinth, grape-hyacinth, freesia, ornamental onion, wood-sorrel, squill, cyclamen, glory-of-the-snow, striped squill, calla lily, gloxinia and tuberous begonia.
- Propagating materials contacted with compounds structure (I) in accordance to this invention also include stems and leaf cuttings.
- a propagating material is coated with a composition comprising the compound of structure (I) and a film former or adhesive agent.
- Compositions that contain a biologically effective amount of a compound of structure (I) and a film former or adhesive agent, can further contain an effective amount of at least one additional biologically active compound or agent.
- examples include compositions comprising (in addition to the compound of structure (I) component and the film former or adhesive agent) an arthropod icides selected from the group consisting of pyrethroids, carbamates, neonicotinoids, neuronal sodium channel blockers, insecticidal macrocyclic lactones, ⁇ -aminobutyric acid (GABA) antagonists, insecticidal ureas and juvenile hormone mimics.
- GABA ⁇ -aminobutyric acid
- compositions comprising (in addition to the compound of structure (I) component and the film former or adhesive agent) at least one additional biologically active compound or agent selected from the group consisting of abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,
- fenpropathrin fenproximate, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, flufenerim (UR-50701 ), flufenoxuron, fonophos,
- halofenozide hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide, nithiazin, novaluron, noviflumuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet,
- pyriproxyfen rotenone, spinosad, spiromesifin (BSN 2060), sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, trichlorfon and triflumuron, aldicarb, oxamyl, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad
- compositions comprising (in addition to the compound of structure (I) component and the film former or adhesive agent) at least one additional biologically active compound or agent selected from fungicides of the group consisting of acibenzolar, azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dichloro-/V-(3-chloro-1 -ethyl- 1 -methyl-2
- prochloraz propamocarb, propiconazole, proquinazid (DPX-KQ926), prothioconazole (JAU 6476), pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil,
- compositions wherein the at least one additional biologically active compound or agent is selected from fungicides in the group consisting of thiram, maneb, mancozeb and captan).
- a propagating material coating comprises a compound of structure (I), a film former or sticking agent.
- the coating may further comprise formulation aids such as a dispersant, a surfactant, a carrier and optionally an antifoam and dye.
- formulation aids such as a dispersant, a surfactant, a carrier and optionally an antifoam and dye.
- the coating not inhibit germination or sprouting of the propagating material.
- the film former or adhesive agent component of the propagating material coating preferably contains an adhesive polymer that may be natural or synthetic and is without phytotoxic effect on the propagating material to be coated.
- the film former or sticking agent can be selected from polyvinyl acetates, polyvinyl acetate copolymers, hydrolyzed polyvinyl acetates, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers, polyvinyl methyl ether, polyvinyl methyl ether-maleic anhydride copolymer, waxes, latex polymers, celluloses including ethylcelluloses and methylcelluloses, hydroxymethylcelluloses, hydroxypropylcellulose, hydroxymethylpropylcelluloses, polyvinylpyrrolidones, alginates, dextrins, malto-dextrins, polysaccharides, fats, oils, proteins, karaya gum, jaguar gum
- lignosulfonates acrylic copolymers, starches, polyvinylacrylates, zeins, gelatin, carboxymethylcellulose, chitosan, polyethylene oxide, acrylimide polymers and copolymers, polyhydroxyethyl acrylate, methylacrylimide monomers, alginate, ethylcellulose, polychloroprene and syrups or mixtures thereof.
- Preferred film formers and adhesive agents include polymers and copolymers of vinyl acetate, polyvinylpyrrolidone-vinyl acetate copolymer and water-soluble waxes. Particularly preferred are polyvinylpyrrolidone-vinyl acetate copolymers and water-soluble waxes.
- the above-identified polymers include those known in the art and for example some are identified as Agrimer® VA 6 and Licowax® KST.
- the amount of film former or sticking agent in the formulation is generally in the range of about 0.001 to 100% of the weight of the propagating material. For large seeds the amount of film former or sticking agent is typically in the range of about 0.05 to 5% of the seed weight; for small seeds the amount is typically in the range of about 1 to 100%, but can be greater than 100% of seed weight in pelleting. For other propagating materials the amount of film former or sticking agent is typically in the range of 0.001 to 2% of the propagating material weight.
- formulation aids may also be used in propagating material treatment coatings of the invention and are well known to those skilled in the art.
- Formulation aids assist in the production or process of propagating material treatment and include, but are not limited, to dispersants, surfactants, carriers, antifoams and dyes.
- Useful dispersants can include highly water-soluble anionic surfactants like BorresperseTM CA, Morwet® D425 and the like.
- Useful surfactants can include highly water-soluble nonionic surfactants like Pluronic® F108, Brij® 78 and the like.
- Useful carriers can include liquids like water and oils which are water-soluble such as alcohols.
- Useful carriers can also include fillers like woodflours, clays, activated carbon, diatomaceous earth, fine-grain inorganic solids, calcium carbonate and the like.
- Clays and inorganic solids which may be used include calcium bentonite, kaolin, china clay, talc, perlite, mica, vermiculite, silicas, quartz powder, montmorillonite and mixtures thereof.
- Antifoams can include water dispersible liquids comprising polyorganic siloxanes like Rhodorsil® 416.
- Dyes can include water dispersible liquid colorant compositions like Pro-lzed® Colorant Red.
- formulation aids include those listed herein and those listed in McCutcheon's 2001, Volume 2: Functional Materials, published by MC Publishing Company.
- the amount of formulation aids used may vary, but generally the weight of the components will be in the range of about 0.001 to 10000% of the propagating material weight, with the percentages above 100% being mainly used for pelleting small seed.
- the amount of formulating aids is about 0.01 to 45% of the seed weight and typically about 0.1 to 15% of the seed weight.
- the amount of formulation aids generally is about 0.001 to 10% of the propagating material weight.
- Dusts or powders may be applied by tumbling the propagating material with a formulation comprising a compound of structure (I) and a sticking agent to cause the dust or powder to adhere to the propagating material and not fall off during packaging or transportation. Dusts or powders can also be applied by adding the dust or powder directly to the tumbling bed of propagating materials, followed by spraying a carrier liquid onto the seed and drying. Dusts and powders comprising the compound can also be applied by treating (e.g., dipping) at least a portion of the propagating material with a solvent such as water, optionally comprising a sticking agent, and dipping the treated portion into a supply of the dry dust or powder.
- a solvent such as water
- Propagating materials can also be dipped into compositions comprising structure (I) formulations of wetted powders, solutions, suspoemulsions, emulfiable concentrates and emulsions in water, and then dried or directly planted in the growing medium.
- structure (I) formulations of wetted powders, solutions, suspoemulsions, emulfiable concentrates and emulsions in water and then dried or directly planted in the growing medium.
- Propagating materials such as bulbs, tubers, corms and rhizomes typically need only a single coating layer to provide a biologically effective amount of a compound of structure (I).
- Propagating materials can also be coated by spraying a suspension concentrate directly into a tumbling bed of propagating materials and then drying the propagating materials.
- other formulation types like wetted powders, solutions, suspoemulsions, emulsifiable concentrates and emulsions in water may be sprayed on the propagating materials. This process is particularly useful for applying film coatings to seeds.
- Propagating materials such as seeds may be presized prior to coating. After coating the propagating materials are dried and then optionally sized by transfer to a sizing machine. These machines are known in the art for example, as a typical machine used when sizing corn (maize) seed in the industry.
- the seed and coating material are mixed in any variety of conventional seed coating apparatus.
- the rate of rolling and coating application depends upon the seed.
- a satisfactory seed coating apparatus comprises a rotating type pan with lifting vanes turned at sufficient rpm to maintain a rolling action of the seed, facilitating uniform coverage.
- the seed coating must be applied over sufficient time to allow drying to minimize clumping of the seed.
- forced air or heated forced air can facilitate an increased rate of application.
- this process can be a batch or continuous process. A continuous process allows the seeds to flow continuously throughout the product run. New seeds enter the pan in a steady stream to replace coated seeds exiting the pan.
- the seed coating process of the present invention is not limited to thin film coating and may also include seed pelleting.
- the pelleting process typically increases the seed weight from 2 to 100 times and can be used to also improve the shape of the seed for use in mechanical seeders.
- Pelleting compositions generally contain a solid diluent, which is typically an insoluble particulate material, such as clay, ground limestone, powdered silica, etc., to provide bulk in addition to a binder such as an artificial polymer (e.g., polyvinyl alcohol, hydrolyzed polyvinyl acetates, polyvinyl methyl ether, polyvinyl methyl ether-maleic anhydride copolymer, and polyvinylpyrrolidone) or natural polymer (e.g., alginates, karaya gum, jaguar gum, tragacanth gum, polysaccharide gum, mucilage). After sufficient layers have been built up, the coat is dried and the pellets graded. A method for producing pellets is
- Seed varieties and seeds with specific transgenic traits can be tested to determine which seed treatment options and application rates may complement such varieties and transgenic traits in order to enhance yield. Further, the good root establishment and early emergence that results from the proper use of the compound of structure (I) seed treatment may result in more efficient nitrogen use, a better ability to withstand drought and an overall increase in yield potential of a variety or varieties containing a certain trait when combined with a seed treatment.
- composition is applied within a foliar formulation.
- Such formulations will generally include at least one additional component selected from the group consisting of
- formulation ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
- Useful formulations include both liquid and solid compositions.
- Liquid compositions include solutions (including emulsifiable
- aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspoemulsion.
- nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
- compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a
- An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
- Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry
- formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
- Liquid and solid formulations can be applied onto seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other subterranean plant parts and/or foliage through systemic uptake.
- Effective foliar formulations will typically contain from about 10 "5 M to 10 "12 M of the composition.
- formulations contain from about 10 "6 M to 10 "10 M of the compound of structure (I).
- the composition is applied to soil either prior to or following planting of plant propagating materials.
- Compositions can be applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants.
- composition of the present invention in the form of a soil drench liquid formulation.
- this method wherein the environment is soil and the composition is applied to the soil as a soil drench formulation.
- Other methods of contact include application of a compound or a composition of the invention by direct and residual sprays, aerial sprays, gels, seed coatings, microencapsulations, systemic uptake, baits, ear tags, boluses, foggers, fumigants, aerosols, dusts and many others.
- One embodiment of a method of contact is a dimensionally stable fertilizer granule, stick or tablet comprising a compound or composition of the invention.
- Effective soil formulations will typically contain from about 10 "5 M to 10 "12 M of the composition. In a preferred embodiment, formulations contain from about 10 "6 M to 10 "10 M of the compound of structure (I).
- Seeds that can be treated include, for example, wheat (Triticum aestivum L), durum wheat (Triticum durum Desf.), barley (Hordeum vulgare L), oat (A vena sativa L), rye (Secale cereale L), maize (Zea mays L), sorghum (Sorghum vulgare Pers.), rice (Oryza sativa L), wild rice (Zizania aquatica L), millet (Eleusine coracana, Panicum miliaceum), cotton (Gossypium barbadense L. and G.
- hirsutum L flax (Linum usitatissimum L), sunflower (Helianthus annuus L), soybean (Glycine max Merr.), garden bean (Phaseolus vulgaris L), lima bean (Phaseolus limensis Macf.), broad bean (Vicia faba L), garden pea (Pisum sativum L), peanut (Arachis hypogaea L), alfalfa (Medicago sativa L), beet (Beta vulgaris L), garden lettuce (Lactuca sativa L), rapeseed (Brassica rapa L. and B.
- cole crops such as cabbage, cauliflower and broccoli (Brassica oleracea L), turnip (Brassica rapa L), leaf (oriental) mustard (Brassica juncea Coss.), black mustard (Brassica nigra Koch), tomato (Lycopersicon esculentum Mill.), potato (Solan urn tuberosum L), pepper (Capsicum frutescens L), eggplant (Solanum melongena L), tobacco (Nicotiana tabacum), cucumber (Cucumis sativus L), muskmelon
- repens L. and G. elegans Bieb. statice (e.g., Limonium sinuatum Mill., L. sinense Kuntze.), blazing star (e.g., Liatris spicata Willd., L.
- pycnostachya Michx. L. scariosa Willd.
- lisianthus e.g., Eustoma grandiflorum (Raf.) Shinn
- yarrow e.g., Achillea filipendulina Lam., A. millefolium L
- marigold e.g., Tagetes patula L, T. erecta L
- pansy e.g., Viola cornuta L, V.
- tricolor L tricolor L
- impatiens e.g., Impatiens balsamina L.
- petunia petunia
- Geranium Garanium spp.
- coleus e.g., Solenostemon scutellarioides (L.) Codd
- seeds, but also rhizomes, tubers, bulbs or corms, including viable cuttings thereof, can be treated according to the invention from, for example, potato (Solanum tuberosum L), sweet potato (Ipomoea batatas L), yam (Dioscorea cayenensis Lam. and D.
- Stem cuttings can be treated according to this invention include those from such plants as sugarcane (Saccharum officinarum L), carnation (Dianthus caryophyllus L), florists
- chrysanthemum Chrysanthemum mortifolium Ramat.
- begonia Begonia spp.
- geranium Gaanium spp.
- coleus e.g., Solenostemon
- Leaf cuttings which can be treated according to this invention include those from begonia (Begonia spp.), african-violet (e.g., Saintpaulia ionantha Wendl.) and sedum (Sedum spp.).
- begonia Bergonia spp.
- african-violet e.g., Saintpaulia ionantha Wendl.
- sedum Sedum spp.
- the above recited cereal, vegetable, ornamental (including flower) and fruit crops are illustrative, and should not be considered limiting in any way.
- preferred embodiments of this invention include wheat, rice, maize, barley, sorghum, oats, rye, millet, soybeans, peanuts, beans, rapeseed, canola, sunflower, sugar cane, potatoes, sweet potatoes, cassava, sugar beets, tomatoes, plantains and bananas, and alfalfa.
- more than one compound of structure (I) may be included. Any number and combination of compounds of structure (I) may be included in the agricultural compositions described.
- THF is tetrahydrofuran
- DMF is dimethylformamide GENERAL METHODS AND MATERIALS
- test compound 25 ml_, 10 "7 M in Dl-water
- aqueous solution of the test compound 25 ml_, 10 "7 M in Dl-water
- Five Petri dishes and 100 soybean seeds were used to test one compound.
- a piece of Whatman filter paper was used to cover the inner side of each Petri dish to allow uniform distribution of testing solution.
- Seeds germinated for 24 hr using the seed germination assay above were left open to light for another 40 hr.
- the radical length was measured and the percentage of germinating seed with radical length of greater than 1 .5 cm was determined.
- the reaction mixture was pumped dry and washed with DI-H 2 O 3 times (1 ml_ each).
- the purified product was dried under vacuum and analyzed with 1 H NMR and LC-MS. 50 mg of product was obtained in a yield of 27% based on the amount of the amine.
- the reaction mixture was pumped dry and washed with DI-H 2 O 3 times (1 mL/each).
- the purified product was dried under vacuum and analyzed with 1 H NMR and LC-MS. 97 mg of product was obtained in a yield of 55% based on the amount of the amine.
- the reaction mixture was pumped dry and washed with DI-H 2 O 3 times (1 mL/each).
- the purified product was dried under vacuum and analyzed with 1 H NMR and LC-MS. 60 mg of product was obtained in a yield of 34% based on the amount of the amine.
- the reaction mixture was pumped dry and washed with DI-H 2 O 3 times (1 mL/each).
- the purified product was dried under vacuum and analyzed with 1 H NMR and LC-MS. 65 mg of product was obtained in a yield of 31 % based on the amount of the amine.
- Example 4 Compound (E)-N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2- methoxytetrahydro-2H-pyran-3-yl)-3-(3-(trifluoromethyl)phenyl)acrylamide prepared in Example 4 was evaluated using the seed germination assay described in General Methods. Soybean seeds treated with this compound showed 75% germination in 24 hours. In the control experiment, soybean seeds showed 48% germination in 24 hours. The standard deviation of these experiments was below 10%.
- DMAP (0.12 g, 0.1 .02 mmol
- EDC HCI 0.2 g, 1 .02 mmol
- (2R,3S,4R,5R,6R)-5- amino-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4-diol (0.15 g, 0.75 mmol) were added and the reaction was stirred overnight at room temperature.
- the reaction is diagrammed in Scheme 5.
- the reaction mixture was pumped dry and washed with DI-H 2 O 3 times (1 mL/each).
- the purified product was dried under vacuum and analyzed with 1 H NMR and LC-MS._The reaction mixture was pumped dry and dissolved in DI-H 2 O (2 ml) and centrifuged. 129 mg of product was obtained in a yield of 66% based on the amount of the phenylpropyoic acid.
- Example 5 N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2- methoxytetrahydro-2H-pyran-3-yl)-3-phenylpropiolamide prepared in Example 5 was evaluated using the seed germination assay described in General Methods. Soybean seeds treated with this compound showed 86% germination in 24 hours. In the control experiment, soybean seeds showed 60% germination in 24 hours. The standard deviation of these experiments was below 10%.
- a comparative testing was done using the sugar structural unit, (2R,3S,4R,5R,6R)-5-amino-2-(hydroxymethyl)-6-methoxytetrahydro-2H- pyran-3,4-diol, to treat soybean seeds.
- the treated soybean seeds showed 53% germination in 24 hours.
- soybean seeds showed 48% germination in 24 hours.
- the standard deviation of these experiments was below 10%.
- Soybean seeds treated with this compound showed 45% of plants with radical length longer than 1 .5 cm after growing at room temperature for an additional 40 hr.
- the control soybean seeds had 45% with radical length longer than 1 .5 cm after growing at room temperature for an additional 40 hr.
- the standard deviation of these experiments was below 10%.
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2014
- 2014-03-06 US US14/770,654 patent/US20160007600A1/en not_active Abandoned
- 2014-03-06 CA CA2904328A patent/CA2904328A1/en not_active Abandoned
- 2014-03-06 WO PCT/US2014/021428 patent/WO2014138490A1/en active Application Filing
- 2014-03-06 BR BR112015021733A patent/BR112015021733A2/en not_active IP Right Cessation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11472981B2 (en) | 2015-09-11 | 2022-10-18 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
Also Published As
Publication number | Publication date |
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US20160007600A1 (en) | 2016-01-14 |
BR112015021733A2 (en) | 2017-07-18 |
CA2904328A1 (en) | 2014-09-12 |
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